DE19521162A1 - N-aryl-1,2,4-triazolin-5-one - Google Patents

Abstract

The present invention relates to the use of partly known N-aryl-1,2,4-triazolin-5-ones of formula (I) in which A, R<1>, R<2>, R<3>, R<4> and R<5> have the meanings given in the description for combatting animal pests.

Description

The present invention relates to the use of partially known N- Aryl-1,2,4-triazolin-5-ones for combating animal pests, in particular insects, arachnids and nematodes, which are used in agriculture, in Forestry, in stock and material protection as well as in the hygiene sector men.

It is already known that certain substituted N-aryl-1,2,4-triazolin-5-one Derivatives have herbicidal properties (see, for example, EP-A-0 610 733 and EP-A- 0 617 026). About an insecticidal action of those known from EP-A-0 617 026 Connections are not known. The verbin known from EP-A-0 610 733 At appropriate application rates, leaf insecticides and acari should be used exhibit zide effectiveness. The insecticidal activity of these compounds is ever yes, especially not at low application rates and concentrations always satisfactory.

It has now been found that the partially known N-aryl-1,2,4-triazolin-5-ones of formula (I)

in which
A represents nitrogen or the group CR,
R represents hydrogen, halogen, nitro, cyano, hydroxy, alkyl which is optionally substituted by halogen, cyano, nitro, alkoxy or amino, optionally substituted cycloalkyl or the radical -CX-NY¹Y²,
R¹ is halogen, nitro, cyano, in each case alkyl or alkoxy optionally substituted by halogen, cyano, nitro, alkoxy or amino, optionally substituted cycloalkyl or the radical -CX-NY¹Y²,
R² represents hydrogen, halogen, alkyl which is optionally substituted by halogen, cyano, nitro, alkoxy or amino or optionally substituted cycloalkyl,
R³ represents nitro, haloalkyl, haloalkoxy or the radical -S (O) _n R⁶,
R⁴ for halogen, nitro, cyano, each optionally substituted by halogen, cyano, nitro, alkoxy or amino-substituted alkyl or alkoxy, for alkenyl, alkenyloxy, alkynyl, hydroxy, mercapto, in each case optionally substituted cycloalkyl or cycloalkylalkyl, in each case optionally substituted aryl, aryloxyalkyl or aralkyl or the radical -S (O) _n R⁶,
R⁵ for hydrogen, cyano, each optionally substituted by halogen, cyano, nitro, alkoxy or amino-substituted alkyl or alkoxy, for alkenyl, alkenyloxy, alkynyl, alkynyloxy, in each case optionally substituted cycloalkyl or cycloalkylalkyl, in each case optionally substituted aryl or aralkyl or one of the radicals - S (O) _n R⁶, -NR⁷R⁸ or -N = CR⁹R¹⁰,
R⁶ represents alkyl optionally substituted by halogen, cyano, nitro, alkoxy or amino, alkenyl, alkanedienyl, alkynyl, optionally substituted cycloalkyl or optionally substituted aryl,
R⁷ represents hydrogen optionally substituted by halogen, cyano, nitro, alkoxy or amino, represents alkenyl, alkynyl, alkoxy, optionally substituted cycloalkyl or optionally substituted aryl,
R⁸ represents hydrogen, optionally substituted by halogen, cyano, nitro, alkoxy or amino alkyl, represents alkenyl, alkynyl, alkoxy, optionally substituted cycloalkyl or optionally substituted aryl,
R⁷ and R⁸ together with the nitrogen atom to which they are attached represent an optionally substituted heterocycle which optionally contains one or more further heteroatoms,
R⁹ represents hydrogen, optionally substituted by halogen, cyano, nitro, alkoxy or amino, represents alkoxy, optionally substituted cycloalkyl or optionally substituted aryl or heterocyclyl,
R¹⁰ represents hydrogen, optionally substituted by halogen, cyano, nitro, alkoxy or amino, alkyl, alkoxy, optionally substituted cycloalkyl or in each case optionally substituted aryl or heterocyclyl,
X represents oxygen or sulfur,
Y¹ represents hydrogen or alkyl,
Y² represents hydrogen or alkyl and
n represents one of the numbers 0, 1 or 2,
are very suitable for controlling animal pests, in particular insects, arachnids and nematodes.

The compounds of formula (I) can, depending on the type of Substituents as geometric and / or optical isomers or mixtures of isomers different composition. The invention relates to both pure isomers as well as the isomer mixtures.

Surprisingly, the N-aryl-1,2,4- triazolin-5-one has a significantly better activity against animal pests gene as the most structurally similar known compounds.  

The N-aryl-1,2,4-triazolin-5-ones which can be used according to the invention are: Formula (I) generally defined.

Preferred substituents or ranges of those in the above and below radicals mentioned formulas are explained below.

A preferably represents nitrogen or the group CR.

R preferably represents hydrogen, fluorine, chlorine, bromine, nitro, cyano, Hydroxy, optionally by fluorine, chlorine, cyano, nitro or C₁-C₂- Alkoxy substituted C₁-C₄-alkyl, optionally by fluorine, chlorine, Bromine, C₁-C₄ alkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkyl or C₁-C₄ halo genalkoxy substituted C₃-C₆-cycloalkyl, or for one of the radicals -CONH₂, -CSNH₂, -CO-NH-C₁-C₄-alkyl, -CS-NH-C₁-C₄-alkyl, -CO-N (C₁- C₄-alkyl) ₂ or -CS-N (C₁-C₄-alkyl) ₂.

R1 is preferably fluorine, chlorine, bromine, nitro, cyano, given in each case if C₁- substituted by fluorine, chlorine, cyano, nitro or C₁-C₂-alkoxy C₄-alkyl or C₁-C₄-alkoxy, optionally by fluorine, chlorine, bromine, C₁- C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy substituted C₃-C₆-cycloalkyl, or for one of the residues -CONH₂, -CSNH₂, -CO-NH-C₁-C₄-alkyl, -CS-NH-C₁-C₄-alkyl, -CO-N (C₁-C₄-Al kyl) ₂ or -CS-N (C₁-C₄-alkyl) ₂.

R² preferably represents hydrogen, fluorine, chlorine, C₁-C₄-alkyl or C₁-C₄- Haloalkyl.

R³ is preferably nitro, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy or for one of the radicals -S-C₁-C₄-haloalkyl, -SO-C₁-C₄-haloalkyl or -SO₂-C₁-C₄ haloalkyl.

R⁴ preferably represents halogen, nitro, cyano, in each case optionally substituted by fluorine, chlorine, cyano, nitro, C₁-C₄-alkoxy or amino-substituted C₁-C₄- alkyl or C₁-C₄-alkoxy, for C₃-C₆-alkenyl, C₃- C₆-alkenyloxy, C₃-C₆- alkynyl, hydroxy, mercapto, each optionally substituted by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-halo genalkoxy-substituted C₃- C₆-cycloalkyl or C₃-C₆-cycloalkyl-C₁-C₄-al kyl, each optionally by halogen, cyano, nitro, C₁-C₄-alkyl, C₁- C--alkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁-C₄-haloalkylthio or phenyl substituted by halogen or C₁-C₄-Al alkyl substituted phenyl, phenyloxy-C₁-C₄-alkyl or phenyl-C₁-C₄-alkyl or for the rest S (O) _n R⁶.

R⁵ preferably represents hydrogen, cyano, in each case optionally substituted by fluorine, chlorine, cyano, nitro, C₁-C₄-alkoxy or amino, C₁-C₄-alkyl or C₁-C₄-alkoxy, for C₃-C₆-alkenyl, C₃-C₆- Alkenyloxy, C₃-C₆-alkynyl, C₃-C₆-alkynyloxy, each optionally substituted by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy substituted C₃- C₆-cycloalkyl or C₃-C₆-cycloalkyl-C₁-C₄-alkyl, optionally by halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkyl, C₁ -C₄-haloalkoxy, C₁-C₄-haloalkyl thio or phenyl optionally substituted by halogen or C₁-C₄-alkyl, phenyl substituted by benzyl optionally substituted by C₁-C₄-alkyl or for one of the radicals -S (O) _n R⁶, - NR⁷R⁸ or -N = CR⁹R¹⁰.

R⁶ preferably represents optionally by fluorine, chlorine, cyano or nitro substituted C₁-C₄-alkyl, for C₃-C₆-alkenyl, C₃-C₆-alkanedienyl, C₃-C₆- Alkynyl, optionally by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄- Alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy substituted C₃- C₆-cycloalkyl, or optionally by halogen, cyano, nitro, C₁-C₄- Alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkyl, C₁-C₄- Halogenalkoxy, C₁-C₄-haloalkylthio or optionally by halogen or C₁-C₄ alkyl substituted phenyl substituted phenyl.

n preferably represents one of the numbers 0, 1 or 2.

R⁷ preferably represents hydrogen, optionally by fluorine, chlorine, cyano, Nitro, amino or C₁-C₄-alkoxy substituted C₁-C₄-alkyl, for C₃-C₆- Alkenyl, C₃-C₆-alkynyl or C₁-C₄-alkoxy, optionally by fluorine, Chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or C₁-C₄- Halogenalkoxy substituted C₃-C₆-cycloalkyl, or optionally by Halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁- C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁-C₄-haloalkylthio or  phenyl optionally substituted by halogen or C₁-C₄-alkyl substituted phenyl.

R⁸ preferably represents hydrogen optionally substituted by fluorine, chlorine, cyano, nitro, amino or C₁-C₄-alkoxy-substituted C₁-C₄-alkyl, for C₃-C₆-alkenyl, C₃-C₆-alkynyl or C₁-C₄-alkoxy, optionally by Fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy-substituted C₃-C₆-cycloalkyl, or optionally halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁-C₄-haloalkylthio or phenyl substituted by halogen or optionally substituted by halogen or C₁-C₄-alkyl or
R⁷ and R⁸ together with the nitrogen atom to which they are attached preferably represent a saturated five- to seven-membered heterocycle with 1 which is optionally substituted by halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₄-alkylthio up to 3 identical or different hetero atoms from the series nitrogen, oxygen and sulfur.

R⁹ preferably represents hydrogen, optionally by fluorine, chlorine, cyano, Nitro, amino or C₁-C₄-alkoxy substituted C₁-C₄-alkyl or for C₁- C₄ alkoxy.

R¹⁰ preferably represents hydrogen, optionally by fluorine, chlorine, cyano, Nitro, amino or C₁-C₄-alkoxy substituted C₁-C₄-alkyl or for C₁- C₄ alkoxy.

A particularly preferably represents nitrogen or the group CR.

R particularly preferably represents hydrogen, fluorine, chlorine, bromine, nitro, Cyano, hydroxy, methyl, ethyl, n- or i-propyl, methoxymethyl, trifluor methyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl or for one of the residues -CONH₂, -CSNH₂, -CONHCH₃, -CSNHCH₃, -CON (CH₃) ₂ or -CSN (CH₃) ₂.

R¹ particularly preferably represents fluorine, chlorine, bromine, nitro, cyano, methyl, Ethyl, n- or i-propyl, methoxymethyl, trifluoromethyl, difluoromethyl,  Chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethoxy, difluoromethoxy, Trifluoroethoxy or for one of the residues -CONH₂, -CSNH₂, -CONHCH₃, -CSNHCH₃, -CON (CH₃) ₂ and -CSN (CH₃) ₂.

R² particularly preferably represents hydrogen, fluorine, chlorine, methyl or Trifluoromethyl.

R³ particularly preferably represents trifluoromethyl, difluoromethyl, chlorodifluor methyl, dichlorofluoromethyl, trifluoromethoxy, difluoromethoxy, chlorodi fluoromethoxy, trifluoromethylsulfenyl, trifluoromethylsulfinyl or trifluor methylsulfonyl.

R⁴ particularly preferably represents chlorine, bromine, nitro, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n- , i-, s- or t-butoxy, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, fluoropropyl, trifluoromethoxy, difluoromethoxy, methoxychloroxy, chlorofluoroxy, chlorofluoroxy, chlorofluoroxy, chlorofluoroxy, chlorofluoroxy, chlorofluoroxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorofluoroxy, chlorofluoroxy, chlorofluoromethyl , Cyanomethyl, allyl, allyloxy, propargyl, hydroxyl, mercapto, each optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy, cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclopentylmethyl, cyclohexyl or cyclohexylmethyl, each optionally by fluorine Chlorine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, methylthio, trifluoromethylthio, nitro or optionally substituted by fluorine, chlorine or methyl substituted phenyl s phenyl, phenoxymethyl or benzyl or for the rest -S (O) _n R⁶.

R⁵ particularly preferably represents hydrogen, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxy ethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoroethyl, fluoropropyl, difluoromethoxy, chlorodifluoromethoxy, dichlorofluoromethoxy, cyanomethyl, allyl, allyloxy, fluorine, propyloxy, propyloxy, propyloxy , Bromine, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy substituted cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclopentylmethyl, cyclohexyl or cyclohexylmethyl, optionally by fluorine, chlorine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, methylthio, trifluoromethylthio, cyano or phenyl substituted by fluorine, chlorine or methyl substituted phenyl, for benzyl or substituted by methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl for one of the residues -S (O) _n R⁶, -NR⁷R⁸ or -N = CR⁹R¹⁰.

R⁶ particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluorme ethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, fluoropropyl, allyl, Allenyl, propargyl, each optionally by fluorine, chlorine, bromine, Methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy substituted Cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclopentylmethyl, cyclo hexyl or cyclohexylmethyl, or optionally by fluorine, chlorine, Methyl, methoxy, trifluoromethyl, trifluoromethoxy, methylthio, trifluor methylthio, cyano, nitro or optionally by fluorine, chlorine or Methyl substituted phenyl substituted phenyl.

n particularly preferably represents one of the numbers 0, 1 or 2.

R⁷ particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy or cyclopropyl.

R⁸ particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy or cyclopropyl or
R⁷ and R⁸ are particularly preferably with the nitrogen atom to which they are attached, in each case optionally substituted by methyl, ethyl, methoxy or ethoxy substituted piperidinyl, piperazinyl or morpholinyl.

R⁹ particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy.

R¹⁰ particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy.  

Some of the compounds of the formula (I) are known (see, for example, EP-A- 0 617 026).

The radicals listed above or listed in preferred areas definitions and explanations apply to the end products and to the initial and intermediates accordingly. These residual definitions can be one below the other which, also between the respective preferred areas, can be combined as desired will.

According to the invention, preference is given to using the compounds of the formula (I) in which a combination of the meanings listed above as preferred gene is present.

According to the invention, the compounds of Formula (I) in which a combination of the above is particularly preferred listed meanings is present.

In the residue definitions listed above and below are hydrocarbons residues such as alkyl or alkenyl - also in compounds with heteroatoms such as Alkoxy or Alylthio - if possible straight or branched.

The N-aryl-1,2,4-triazolin-5-ones which can be used according to the invention are new Formula (Ia)

in which
A¹ represents nitrogen or the group CR ^O ,
R ^{O represents} hydrogen, halogen, nitro, cyano, hydroxyl, alkyl which is optionally substituted by halogen, cyano, nitro, alkoxy or amino, optionally substituted cycloalkyl or the radical -CX¹-NY¹¹Y¹²,
R¹¹ represents halogen, nitro, cyano, in each case alkyl or alkoxy optionally substituted by halogen, cyano, nitro, alkoxy or amino, optionally substituted cycloalkyl or the radical -CX¹-NY¹¹Y¹²,
R 12 represents hydrogen, halogen, alkyl which is optionally substituted by halogen, cyano, nitro, alkoxy or amino or optionally substituted cycloalkyl,
R¹³ represents nitro, haloalkyl, haloalkoxy or the radical -S (O) _n ¹R¹⁶,
R¹⁴ for halogen, cyano, each optionally substituted by halogen, cyano, nitro, alkoxy or amino-substituted alkyl or alkoxy, for alkenyl, alkenyloxy, alkynyl, hydroxy, mercapto, in each case optionally substituted cycloalkyl or cycloalkylalkyl, in each case optionally substituted aryl, aryloxyalkyl or aralkyl or the radical -S (O) _n ¹R¹⁶,
R¹⁵ for hydrogen, cyano, amino, each optionally substituted by halogen, cyano, nitro, alkoxy or amino-substituted alkyl or alkoxy, for alkenyl, alkenyloxy, alkynyl, alkynyloxy, in each case optionally substituted cycloalkyl or cycloalkylalkyl, in each case optionally substituted aryl or aralkyl or one the radicals -S (O) _n ¹R¹⁶, -NR¹⁷R¹⁸ or -N = CR¹⁹R²⁰,
R¹⁶ represents alkyl optionally substituted by halogen, cyano, nitro, alkoxy or amino, alkenyl, alkanedienyl, alkynyl, optionally substituted cycloalkyl or optionally substituted aryl,
R¹⁷ and R¹⁸ together with the nitrogen atom to which they are attached represent an optionally substituted heterocycle which optionally contains one or more further heteroatoms,
R¹⁹ represents hydrogen, optionally substituted by halogen, cyano, nitro, alkoxy or amino, alkyl, alkoxy, optionally substituted cycloalkyl or in each case optionally substituted aryl or heterocyclyl,
R²⁰ represents hydrogen, optionally substituted by halogen, cyano, nitro, alkoxy or amino, represents alkoxy, optionally substituted cycloalkyl or optionally substituted aryl or heterocyclyl,
X¹ represents oxygen or sulfur,
Y¹¹ represents hydrogen or alkyl,
Y¹² represents hydrogen or alkyl and
n¹ represents one of the numbers 0, 1 or 2.

The compounds of formula (Ia) can, depending on the type of Substituents as geometric and / or optical isomers or mixtures of isomers different composition. The invention relates to both pure isomers as well as the isomer mixtures.

It was also found that one

• a) N-aryl-1,2,4-triazolin-5-ones of the formula (Ia) in which
  R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and A¹ have the meaning given above,
  get when one
  1H-triazolinones of the formula (II) in which
  R¹⁴ and R¹⁵ have the meaning given above,
  with halogen derivatives of the formula (III) in which
  R¹¹, R¹², R¹³ and A¹ have the meaning given above and
  Hal stands for halogen,
  if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary;
  or
• b) N-aryl-1,2,4-triazolin-5-ones of the formula (Ib) in which
  R¹¹, R¹², R¹³ and A¹ have the meaning given above and
  R ^{14-1 represents} cyano, in each case optionally substituted by halogen, cyano, nitro, alkoxy or amino, alkyl or alkoxy, represents alkenyl, alkenyloxy, alkynyl, in each case optionally substituted cycloalkyl or cycloalkylalkyl or in each case optionally substituted aryl, aryloxyalkyl or aralkyl,
  get when one
  Hydrazine derivatives of the formula (IV) in which
  R¹¹, R¹², R¹³ and A¹ have the meaning given above,
  with imino carboxylic esters of the formula (V) in which
  R ^{14-1 has} the meaning given above and
  R²¹ and R²² independently of one another are alkyl (preferably C₁-C₅-alkyl),
  in the presence of a diluent;
  or
• c) N-aryl-1,2,4-triazolin-5-ones of the formula (Ic) in which
  R¹¹, R¹², R¹³, R¹⁴ and A¹ have the meaning given above and
  R ^{15-1 represents} cyano, optionally substituted by halogen, cyano, nitro, alkoxy or amino, represents alkenyl, alkynyl, in each case optionally substituted cycloalkyl and cycloalkylalkyl or optionally substituted aryl,
  get when one
  N-aryl-1,2,4-triazolin-5-ones of the formula (Id) in which
  R¹¹, R¹², R¹³, R¹⁴ and A¹ have the meaning given above,
  with alkylating agents of the formula (VI) ER ^15-1 (VI) in which
  R ^{15-1 has} the meaning given above and
  E represents an electron-withdrawing leaving group,
  if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary.

The new N-aryl-1,2,4-triazolin-5-ones according to the invention are of the formula (Ia) generally defined.

Preferred substituents or ranges of those in the above and below radicals mentioned formulas are explained below.

A¹ preferably represents nitrogen or the group CR ^O.

R ^O preferably represents hydrogen, fluorine, chlorine, bromine, nitro, cyano, hydroxy, optionally substituted by fluorine, chlorine, cyano, nitro or C₁-C₂- alkoxy-substituted C₁-C₄-alkyl, optionally by fluorine, chlorine, bromine, C₁ -C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-halo genalkoxy substituted C₃-C₆-cycloalkyl, or for one of the residues -CONH₂, -CSNH₂, -CO-NH-C₁-C₄- Alkyl, -CS-NH-C₁-C₄-alkyl, -CO-N (C₁-C₄-alkyl) ₂ or -CS-N (C₁-C₄-alkyl) ₂.

R¹¹ preferably represents fluorine, chlorine, bromine, nitro, cyano, given in each case if C₁- substituted by fluorine, chlorine, cyano, nitro or C₁-C₂-alkoxy C₄-alkyl or C₁-C₄-alkoxy, optionally by fluorine, chlorine, bromine, C₁- C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy substituted C₃-C₆-cycloalkyl, or for one of the residues -CONH₂, -CSNH₂, -CO-NH-C₁-C₄-alkyl, -CS-NH-C₁-C₄-alkyl, -CO-N (C₁-C₄-Al kyl) ₂ or -CS-N (C₁-C₄-alkyl) ₂.

R¹² preferably represents hydrogen, fluorine, chlorine, C₁-C₄-alkyl or C₁-C₄- Haloalkyl.

R¹³ is preferably nitro, C₁-C₄ haloalkyl, C₁-C₄ haloalkoxy or for one of the radicals -S-C₁-C₄-haloalkyl, -SO-C₁-C₄-haloalkyl or -SO₂-C₁-C₄ haloalkyl.  

R¹⁴ preferably represents halogen, cyano, in each case optionally substituted by fluorine, chlorine, cyano, nitro, C₁-C₄-alkoxy or amino, C₁-C₄-alkyl or C₁-C₄-alkoxy, for C₃-C₆-alkenyl, C₃-C₆- Alkenyloxy, C₃-C₆-alkynyl, hydroxy, mercapto, each optionally substituted by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy-substituted C₃-C₆-cycloalkyl or C₃-C₆-cycloalkyl-C₁-C₄-alkyl, each optionally by halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkyl, C₁-C₄- Halogenalkoxy, C₁-C₄-Halo genalkylthio or optionally substituted by halogen or C₁-C₄-alkyl substituted phenyl, phenyloxy-C₁-C₄-alkyl or phenyl-C₁-C₄-alkyl or for the rest S (O) _n ¹R¹⁶.

R¹⁵ preferably represents hydrogen, cyano, amino, in each case optionally substituted by fluorine, chlorine, cyano, nitro, C₁-C₄-alkoxy or amino-substituted C₁-C₄-alkyl or C₁-C₄-alkoxy, for C₃-C₆-alkenyl, C₃- C₆-alkenyloxy, C₃-C₆-alkynyl, C₃-C₆-alkynyloxy, each optionally substituted by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy substituted C₃ -C₆-cycloalkyl or C₃-C₆-cycloalkyl-C₁- C₄-alkyl, optionally by halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkyl, C₁ -C₄-haloalkoxy, C₁-C₄-haloalkylthio or phenyl which is optionally substituted by halogen or C₁-C₄-alkyl, phenyl which is optionally substituted by C₁-C₄-alkyl or for one of the radicals S (O) _n ¹R¹⁶, -NR¹⁷R¹⁸ or - N = CR¹⁹R²⁰.

R¹⁶ preferably represents optionally by fluorine, chlorine, cyano or nitro substituted C₁-C₄-alkyl, for C₃-C₆-alkenyl, C₃-C₆-alkanedienyl, C₃-C₆- Alkynyl, optionally by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄- Alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy substituted C₃- C₆-cycloalkyl, or optionally by halogen, cyano, nitro, C₁-C₄- Alkyl, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkyl, C₁-C₁ halo genalkoxy, C₁-C₄-haloalkylthio or optionally by halogen or C₁-C₄ alkyl substituted phenyl substituted phenyl.

n 1 is preferably one of the numbers 0, 1 or 2.  

R¹⁷ and R¹⁸ are preferably together with the nitrogen atom to which they are attached are bound, optionally by halogen, C₁-C₄-alkyl, C₁- C₄-Alkoxy or C₁-C₄-alkylthio substituted, saturated five to seven membered heterocycle with 1 to 3 identical or different hetero atoms from the series nitrogen, oxygen and sulfur.

R¹⁹ preferably represents hydrogen, optionally by fluorine, chlorine, cyano, Nitro, amino or C₁-C₄-alkoxy substituted C₁-C₄-alkyl or for C₁- C₄ alkoxy.

R²⁰ preferably represents hydrogen, optionally by fluorine, chlorine, cyano, Nitro, amino or C₁-C₄-alkoxy substituted C₁-C₄-alkyl or for C₁- C₄ alkoxy.

A¹ particularly preferably represents nitrogen or the group CR ^O.

R ^O particularly preferably represents hydrogen, fluorine, chlorine, bromine, nitro, cyano, hydroxy, methyl, ethyl, n- or i-propyl, methoxymethyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl or one of the radicals -CONH₂, -CSNH₂ , -CONHCH₃, -CSNHCH₃, -CON (CH₃) ₂ or -CSN (CH₃) ₂.

R¹¹ particularly preferably represents fluorine, chlorine, bromine, nitro, cyano, methyl, Ethyl, n- or i-propyl, methoxymethyl, trifluoromethyl, difluoromethyl, Chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethoxy, difluoromethoxy, Trifluoroethoxy or for one of the residues -CONH₂, -CSNH₂, -CONHCH₃, -CSNHCH₃, -CON (CH₃) ₂ and -CSN (CH₃) ₂.

R 12 is particularly preferably hydrogen, fluorine, chlorine, methyl or Trifluoromethyl.

R¹³ particularly preferably represents trifluoromethyl, difluoromethyl, chlorodifluor methyl, dichlorofluoromethyl, trifluoromethoxy, difluoromethoxy, chlorodi fluoromethoxy, trifluoromethylsulfenyl, trifluoromethylsulfinyl or trifluor methylsulfonyl.  

R¹⁴ particularly preferably represents chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i -, s- or t-butoxy, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichloro fluoromethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, fluoropropyl, trifluoromethoxy, difluoromethoxy, chlorodifluoromethoxy, Dichlorfluor methoxy, trifluoroethoxy, tetrafluoroethoxy, pentafluoroethoxy, cyanomethyl , Allyl, allyloxy, propargyl, hydroxyl, mercapto, each optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy, cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclopentylmethyl, cyclohexyl or cyclohexylmethyl, each optionally by fluorine, chlorine, Methyl, methoxy, trifluoromethyl, trifluoromethoxy, methylthio, trifluoromethylthio, nitro or Phe substituted by phenyl optionally substituted by fluorine, chlorine or methyl nyl, phenoxymethyl or benzyl or for the rest -S (O) _n ¹R¹⁶.

R¹⁵ particularly preferably represents hydrogen, cyano, amino, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i -, S- or t-butoxy, methoxymethyl, methoxyethyl, ethoxy methyl, ethoxyethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoroethyl, fluoropropyl, difluoromethoxy, chlorodifluoromethoxy, dichlorofluoromethoxy, cyanomethyl, allyl, allyloxy, propyl paroxy cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclopentylmethyl, cyclohexyl or cyclohexylmethyl substituted by fluorine, chlorine, bromine, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy, optionally by fluorine, chlorine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, methylthio, trifluoromethylthio Nitro and phenyl substituted by fluorine, chlorine or methyl, optionally substituted by phenyl, for optionally substituted by methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl Benzyl or for one of the radicals -S (O) _n ¹R¹⁶, -NR¹⁷R¹⁸ or -N = CR¹⁹R²⁰.

R¹⁶ particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluorme ethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, fluoropropyl, allyl, Allenyl, propargyl, each optionally by fluorine, chlorine, bromine, Methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy substituted  Cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclopentylmethyl, cyclo hexyl or cyclohexylmethyl, or optionally by fluorine, chlorine, Methyl, methoxy, trifluoromethyl, trifluoromethoxy, methylthio, trifluor methylthio, cyano, nitro or optionally by fluorine, chlorine or Methyl substituted phenyl substituted phenyl.

n 1 particularly preferably represents one of the numbers 0, 1 or 2.

R¹⁷ and R¹⁸ are particularly preferably with the nitrogen atom to which they are attached are bound, each optionally by methyl, ethyl, methoxy or ethoxy substituted piperidinyl, piperazinyl or morpholinyl.

R¹⁹ particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy.

R²⁰ particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy.

The radicals listed above or listed in preferred areas definitions and explanations apply to the end products and to the initial and intermediates accordingly. These residual definitions can be one below the other which, also between the respective preferred areas, can be combined as desired will.

According to the invention, preference is given to the compounds of the formula (I) in which a combination of those listed as preferred (preferred) above Meanings exist.

According to the invention, particular preference is given to the compounds of the formula (I), in which are a combination of those listed as particularly preferred above Meanings exist.

In the residue definitions listed above and below are hydrocarbons residues such as alkyl or alkenyl - also in compounds with heteroatoms such as Alkoxy or Alylthio - if possible straight or branched.  

Examples of the new compounds according to the invention are in Tables 1a listed up to 80d:

Table 1a

Compounds in Table 1a correspond to the general formula (IA), in which
R¹⁴ = CH₃
R¹⁵ = CH₃ and
Ar = as listed below:

Table 1b

Table 1b contains the compounds of the general formula (IA), in which
R¹⁴ = CH₃
R¹⁵ = CH₃ and
Ar = as listed below:

Table 1c

Table 1c contains the compounds of the general formula (IA), in which
R¹⁴ = CH₃
R¹⁵ = CH₃ and
Ar = as listed below:

Table 1d

Table 1d contains the compounds of the general formula (IA), in which
R¹⁴ = CH₃
R¹⁵ = CH₃ and
Ar = as listed below:

Tables 2a to 2d

Tables 2a to 2d contain the compounds of the general formula (IA) in which
R¹⁴ = C₂H₅
R¹⁵ = CH₃ and
Ar = as listed in Tables 1a to 1d.

Tables 3a to 3d

Tables 3a to 3d contain the compounds of the general formula (IA) in which
R¹⁴ = C₃H₇-i
R¹⁵ = CH₃ and
Ar = as listed in Tables 1a to 1d.

Tables 4a to 4d

Tables 4a to 4d contain the compounds of the general formula (IA), in which
R¹⁴ = C₃H₇-n
R¹⁵ = CH₃ and
Ar = as listed in Tables 1a to 1d.

Tables 5a to 5d

Tables 5a to 5d contain the compounds of the general formula (IA), in which
R¹⁴ = C₄H₉-n
R¹⁵ = CH₃ and
Ar = as listed in Tables 1a to 1d.

Tables 6a to 6d

Tables 6a to 6d contain the compounds of the general formula (IA), in which

R¹⁵ = CH₃ and
Ar = as listed in Tables 1a to 1d.

Tables 7a to 7d

Tables 7a to 7d contain the compounds of the general formula (IA), in which

R¹⁵ = C₂H₅ and
Ar = as listed in Tables 1a to 1d.

Tables 8a to 8d

Tables 8a to 8d contain the compounds of the general formula (IA), in which

R¹⁵ = C₃H₇-i and
Ar = as listed in Tables 1a to 1d.

Tables 9a to 9d

Tables 9a to 9d contain the compounds of the general formula (IA), in which

Ar = as listed in Tables 1a to 1d.

Tables 10a to 10d

Tables 10a to 10d contain the compounds of the general formula (IA), in which
R¹⁴ = C₃H₇-i

Ar = as listed in Tables 1a to 1d.

Tables 11a to 11d

Tables 11a to 11d contain the compounds of the general formula (IA), in which
R¹⁴ = C₄H₉-t

Ar = as listed in Tables 1a to 1d.  

Tables 12a to 12d

Tables 12a to 12d contain the compounds of the general formula (IA), in which

R¹⁵ = -CH₂CH₂OCH₃ and
Ar = as listed in Tables 1a to 1d.

Tables 13a to 13d

Tables 13a to 13d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃
R¹⁵ = H and
Ar = as listed in Tables 1a to 1d.

Tables 14a to 14d

Tables 14a to 14d contain the compounds of the general formula (IA) in which
R¹⁴ = CF₃
R¹⁵ = -SCFCl₂ and
Ar = as listed in Tables 1a to 1d.

Tables 15a to 15d

Tables 15a to 15d contain the compounds of the general formula (IA), in which

R¹⁵ = -OCH₃ and
Ar = as listed in Tables 1a to 1d.

Tables 16a to 16d

Tables 16a to 16d contain the compounds of the general formula (IA) in which

R¹⁵ = -OC₂H₅ and
Ar = as listed in Tables 1a to 1d.

Tables 17a to 17d

Tables 17a to 17d contain the compounds of the general formula (IA), in which

R¹⁵ = -OCH₂CH = CH₂ and
Ar = as listed in Tables 1a to 1d.

Tables 18a to 18d

Tables 18a to 18d contain the compounds of the general formula (IA), in which

R¹⁵ = -NH₂ and
Ar = as listed in Tables 1a to 1d.

Tables 19a to 19d

Tables 19a to 19d contain the compounds of the general formula (IA), in which

R¹⁵ = -CHF₂ and
Ar = as listed in Tables 1a to 1d.

Tables 20a to 20d

Tables 20a to 20d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃
R¹⁵ = C₃H₇-i and
Ar = as listed in Tables 1a to 1d.

Tables 21a to 21d

Tables 21a to 21d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃
R¹⁵ = CH₃ and
Ar = as listed in Tables 1a to 1d.

Tables 22a to 22d

Tables 22a to 22d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃
R¹⁵ = C₂H₅ and
Ar = as listed in Tables 1a to 1d.

Tables 23a to 23d

Tables 23a to 23d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃
R¹⁵ = C₄H₉-t and
Ar = as listed in Tables 1a to 1d.

Tables 24a to 24d

Tables 24a to 24d contain the compounds of the general formula (IA) in which
R¹⁴ = CF₃

Ar = as listed in Tables 1a to 1d.

Tables 25a to 25d

Tables 25a to 25d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃

Ar = as listed in Tables 1a to 1d.

Tables 26a to 26d

Tables 26a to 26d contain the compounds of the general formula (IA), in which
R¹⁴ = CHF₂

Ar = as listed in Tables 1a to 1d.  

Tables 27a to 27d

Tables 27a to 27d contain the compounds of the general formula (IA), in which
R¹⁴ = CHF₂
R¹⁵ = CN and
Ar = as listed in Tables 1a to 1d.

Tables 28a to 28d

Tables 28a to 28d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃
R¹⁵ = CN and
Ar = as listed in Tables 1a to 1d.

Tables 29a to 29d

Tables 29a to 29d contain the compounds of the general formula (IA) in which
R¹⁴ = SCHF₂
R¹⁵ = C₃H₇-i and
Ar = as listed in Tables 1a to 1d.

Tables 30a to 30d

Tables 30a to 30d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃
R¹⁵ = -OCH₃ and
Ar = as listed in Tables 1a to 1d.

Tables 31a to 31d

Tables 31a to 31d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃
R¹⁵ = -CH₂CH₂OCH₃ and
Ar = as listed in Tables 1a to 1d.

Tables 32a to 32d

Tables 32a to 32d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃

Ar = as listed in Tables 1a to 1d.  

Tables 33a to 33d

Tables 33a to 33d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃

Ar = as listed in Tables 1a to 1d.

Tables 34a to 34d

Tables 34a to 34d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃

Ar = as listed in Tables 1a to 1d.

Tables 35a to 35d

Tables 35a to 35d contain the compounds of the general formula (IA), in which
R¹⁴ = -OCH₂CF₃

Ar = as listed in Tables 1a to 1d.  

Tables 36a to 36d

Tables 36a to 36d contain the compounds of the general formula (IA), in which

Ar = as listed in Tables 1a to 1d.

Tables 37a to 37d

Tables 37a to 37d contain the compounds of the general formula (IA), in which
R¹⁴ = -CF₂CF₃

Ar = as listed in Tables 1a to 1d.

Tables 38a to 38d

Tables 38a to 38d contain the compounds of the general formula (IA), in which
R¹⁴ = -CF₂CF₃
R¹⁵ = C₄H₉-t and
Ar = as listed in Tables 1a to 1d.

Tables 39a to 39d

Tables 39a to 39d contain the compounds of the general formula (IA), in which
R¹⁴ = -CF₂CF₃
R¹⁵ = C₃H₇-i and
Ar = as listed in Tables 1a to 1d.

Tables 40a to 40d

Tables 40a to 40d contain the compounds of the general formula (IA), in which
R¹⁴ = -CF₂CF₃
R¹⁵ = C₂H₅ and
Ar = as listed in Tables 1a to 1d.

Tables 41a to 41d

Tables 41a to 41d contain the compounds of the general formula (IA), in which
R¹⁴ = -CF₂CF₃
R¹⁵ = CH₃ and
Ar = as listed in Tables 1a to 1d.

Tables 42a to 42d

Tables 42a to 42d contain the compounds of the general formula (IA), in which
R¹⁴ = -CF₂CHF₂
R¹⁵ = CH₃ and
Ar = as listed in Tables 1a to 1d.

Tables 43a to 43d

Tables 43a to 43d contain the compounds of the general formula (IA), in which
R¹⁴ = -CF₂CHF₂
R¹⁵ = C₂H₅ and
Ar = as listed in Tables 1a to 1d.

Tables 44a to 44d

Tables 44a to 44d contain the compounds of the general formula (IA), in which
R¹⁴ = -CF₂CHF₂
R¹⁵ = C₃H₇-i and
Ar = as listed in Tables 1a to 1d.

Tables 45a to 45d

Tables 45a to 45d contain the compounds of the general formula (IA), in which
R¹⁴ = -CF₂CHF₂
R¹⁵ = C₄H₉-t and
Ar = as listed in Tables 1a to 1d.

Tables 46a to 46d

Tables 46a to 46d contain the compounds of the general formula (IA), in which
R¹⁴ = -CF₂CHF₂
R¹⁵ = C₃H₇-n and
Ar = as listed in Tables 1a to 1d.

Tables 47a to 47d

Tables 47a to 47d contain the compounds of the general formula (IA), in which
R¹⁴ = -CF₂CHF₂

Ar = as listed in Tables 1a to 1d.  

Tables 48a to 48d

Tables 48a to 48d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃
R¹⁵ = -CH₂CH₂CH₂F and
Ar = as listed in Tables 1a to 1d.

Tables 49a to 49d

Tables 49a to 49d contain the compounds of the general formula (IA), in which
R¹⁴ = C₃H₇-i
R¹⁵ = -CH₂CH₂CH₂F and
Ar = as listed in Tables 1a to 1d.

Tables 50a to 50d

Tables 50a to 50d contain the compounds of the general formula (IA), in which

R¹⁵ = -CH₂CH₂CH₂F and
Ar = as listed in Tables 1a to 1d.

Tables 51a to 51d

Tables 51 a to 51 d contain the compounds of the general formula (IA), in which
R¹⁴ = CN
R¹⁵ = -CH₂CH₂CH₂F and
Ar = as listed in Tables 1a to 1d.

Tables 52a to 52d

Tables 52a to 52d contain the compounds of the general formula (IA), in which
R¹⁴ = CN
R′⁵ = -CHF₂ and
Ar = as listed in Tables 1a to 1d.

Tables 53a to 53d

Tables 53a to 53d contain the compounds of the general formula (IA), in which
R¹⁴ = CN

Ar = as listed in Tables 1a to 1d.  

Tables 54a to 54d

Tables 54a to 54d contain the compounds of the general formula (IA) in which
R¹⁴ = Br

Ar = as listed in Tables 1a to 1d.

Tables 55a to 55d

Tables 55a to 55d contain the compounds of the general formula (IA), in which
R¹⁴ = Cl

Ar = as listed in Tables 1a to 1d.

Tables 56a to 56d

Tables 56a to 56d contain the compounds of the general formula (IA), in which
R¹⁴ = Cl
R¹⁵ = -CHF₂ and
Ar = as listed in Tables 1a to 1d.

Tables 57a to 57d

Tables 57a to 57d contain the compounds of the general formula (IA), in which
R¹⁴ = Cl
R¹⁵ = -CH₃ and
Ar = as listed in Tables 1a to 1d.

Tables 58a to 58d

Tables 58a to 58d contain the compounds of the general formula (IA), in which
R¹⁴ = Cl
R¹⁵ = -C₂H₅ and
Ar = as listed in Tables 1a to 1d.

Tables 59a to 59d

Tables 59a to 59d contain the compounds of the general formula (IA), in which
R¹⁴ = Cl
R¹⁵ = -C₃H₇-i and
Ar = as listed in Tables 1a to 1d.

Tables 60a to 60d

Tables 60a to 60d contain the compounds of the general formula (IA), in which
R¹⁴ = Br
R¹⁵ = -C₃H₇-i and
Ar = as listed in Tables 1a to 1d.

Tables 61a to 61d

Tables 61a to 61d contain the compounds of the general formula (IA), in which
R¹⁴ = Br
R¹⁵ = -C₄H₇-t and
Ar = as listed in Tables 1a to 1d.

Tables 62a to 62d

Tables 62a to 62d contain the compounds of the general formula (IA), in which
R¹⁴ = SCHF₂

Ar = as listed in Tables 1a to 1d.  

Tables 63a to 63d

Tables 63a to 63d contain the compounds of the general formula (IA), in which
R¹⁴ = OCF₂H

Ar = as listed in Tables 1a to 1d.

Tables 64a to 64d

Tables 64a to 64d contain the compounds of the general formula (IA), in which
R¹⁴ = OCHF₂
R¹⁵ = C₄H₉-t
Ar = as listed in Tables 1a to 1d.

Tables 65a to 65d

Tables 65a to 65d contain the compounds of the general formula (IA), in which
R¹⁴ = -OCH₃

Ar = as listed in Tables 1a to 1d.  

Tables 66a to 66d

Tables 66a to 66d contain the compounds of the general formula (IA), in which
R¹⁴ = -OC₂H₅

Ar = as listed in Tables 1a to 1d.

Tables 67a to 67d

Tables 67a to 67d contain the compounds of the general formula (IA), in which
R¹⁴ = -OC₃H₇-i

Ar = as listed in Tables 1a to 1d.

Tables 68a to 68d

Tables 68a to 68d contain the compounds of the general formula (IA), in which
R¹⁴ = -SCH₃

Ar = as listed in Tables 1a to 1d.  

Tables 69a to 69d

Tables 69a to 69d contain the compounds of the general formula (IA), in which
R¹⁴ = -SO₂CH₃

Ar = as listed in Tables 1a to 1d.

Tables 70a to 70d

Tables 70a to 70d contain the compounds of the general formula (IA), in which
R¹⁴ = -SC₃H₇-i

Ar = as listed in Tables 1a to 1d.

Tables 71a to 71d

Tables 71a to 71d contain the compounds of the general formula (IA), in which
R¹⁴ = C₄H₉-t
R¹⁵ = CN and
Ar = as listed in Tables 1a to 1d.

Tables 72a to 72d

Tables 72a to 72d contain the compounds of the general formula (IA), in which
R¹⁴ = -SC₂H₅
R¹⁵ = -CN and
Ar = as listed in Tables 1a to 1d.

Tables 73a to 73d

Tables 73a to 73d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃
R¹⁵ = -CHF₂ and
Ar = as listed in Tables 1a to 1d.

Tables 74a to 74d

Tables 74a to 74d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃
R¹⁵ = -CH₂CN and
Ar = as listed in Tables 1a to 1d.

Tables 75a to 75d

Tables 75a to 75d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃

Ar = as listed in Tables 1a to 1d.

Tables 76a to 76d

Tables 76a to 76d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃

Ar = as listed in Tables 1a to 1d.

Tables 77a to 77d

Tables 77a to 77d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃
R¹⁵ = -N = CHOC₂C₅ and
Ar = as listed in Tables 1a to 1d.

Tables 78a to 78d

Tables 78a to 78d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃

Ar = as listed in Tables 1a to 1d.

Tables 79a to 79d

Tables 79a to 79d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃

Ar = as listed in Tables 1a to 1d.

Tables 80a to 80d

Tables 80a to 80d contain the compounds of the general formula (IA), in which
R¹⁴ = CF₃
R¹⁵ = -SO₂CF₂CH₃
Ar = as listed in Tables 1a to 1d.

If, for example, 2,6-dichloro-4-trifluoromethyl-fluorobenzene and 3- Cyano-4-cyclopropyl-1H-1,2,4-triazolin-5-one as starting materials, so the Reaction flow of the method (a) according to the invention by the following Formula scheme are reproduced:

If, for example, 2,6-dinitro-4-trifluoromethyl-phenyl-hydrazine and N- Methoxycarbonyl-acetimidic acid ester as starting materials, the reaction can run of the method (b) according to the following formula are reproduced:

For example, if 1- (2,6-dichloro-4-trifluoromethyl-phenyl) -3-methyl- (4H) -1,2,4-triazolin-5-one and chlorodifluoromethane as starting materials, so the Reaction flow of the method (c) according to the invention by the following Formula scheme are reproduced:

Those used to carry out process (a) according to the invention as starting materials required 1H-triazolinones are generally defined by the formula (II). In this formula (II) R¹⁴ and R¹⁵ are preferably and particularly preferably  those leftovers that are already related to the description of the Compounds of formula (Ia) according to the invention as preferred or special were preferred for these substituents.

The 1H-triazolinones of the formula (II) are known or can be obtained by known Process (see e.g. EP 283 876; EP 305 844; EP 341 489; EP 415 196; EP 422 469; EP 425 948; EP 431 291; EP 507 171; EP 513 621; EP 534 266; Chem. Ber. 102, 755-766 [1969]; Liebigs Ann. Chem. 343, 24 [1905]). Sometimes they are too Subject of a separate patent application that has not yet been published (cf. German patent application P 4 435 547 from 05.10.1994).

Examples of the 1H-triazolinones of the formula (II) are in Tables (II-1) to (II-49) listed:

Table (II-1)

Compounds in table (II-1) correspond to the general formula (II), in which
R¹⁴ = CH₃ and
R¹⁵ = as listed below:
H, CH₃, C₂H₅, n-C₃H₇, i-C₃H₇, n-C₄H₉, i-C₄H₉, s-C₄H₉, t-C₄H₉, CHF₂, CClF₂, CHClF,
CH₂CH₂CH₂F, CH₂CF₃, CHF = CClF, CH₂CH₂-O-CH₃, CH₂CH₂-O-CH₂CH₃,
CH₂CH = CH₂, CH₂CH₂CH₂-O-CH₃, CH₂CN, CN, CH₂C≡CH, O-CH₃, O-C₂H₅,
O-CH₂CH = CH₂, O-CH (CH₃) C≡CH, SCFCl₂, SO₂CF₂CH₃, N = CHOC₂H₅,
N = C (CH₃) OC₂H₅, NH₂,

Table (II-2)

Table (II-2) contains the compounds of the general formula (II), in which
R¹⁴ = C₂H₅ and
R¹⁵ = as listed in Table (II-1).

Table (II-3)

Table (II-3) contains the compounds of the general formula (II), in which
R¹⁴ = C₃H₇-i and
R¹⁵ = as listed in Table (II-1).

Table (II-4)

Table (II-4) contains the compounds of the general formula (II) in which
R¹⁴ = C₃H₇-n and
R¹⁵ = as listed in Table (II-1).

Table (II-5)

Table (II-5) contains the compounds of the general formula (II), in which
R¹⁴ = C₄H₉-n and
R¹⁵ = as listed in Table (II-1).

Table (II-6)

Table (II-6) contains the compounds of the general formula (II) in which
R¹⁴ = C₄H₉-i and
R¹⁵ = as listed in Table (II-1).

Table (II-7)

Table (II-7) contains the compounds of the general formula (II), in which
R¹⁴ = C₄H₉-t and
R¹⁵ = as listed in Table (II-1).

Table (II-8)

Table (II-8) contains the compounds of the general formula (II), in which
R¹⁴ = C₄H₉-s and
R¹⁵ = as listed in Table (II-1).

Table (II-9)

Table (II-9) contains the compounds of the general formula (II), in which

R¹⁵ = as listed in Table (II-1).

Table (II-10)

Table (II-10) contains the compounds of the general formula (II), in which
R¹⁴ = CF₃ and
R¹⁵ = as listed in Table (II-1).

Table (II-11)

Table (II-11) contains the compounds of the general formula (II), in which
R¹⁴ = CHF₂ and
R¹⁵ = as listed in Table (II-1).

Table (II-12)

Table (II-12) contains the compounds of the general formula (II), in which
R¹⁴ = CClF₂ and
R¹⁵ = as listed in Table (II-1).

Table (II-13)

Table (II-13) contains the compounds of the general formula (II), in which
R¹⁴ = CF₂CF₃ and
R¹⁵ = as listed in Table (II-1).

Table (II-14)

Table (II-14) contains the compounds of the general formula (II), in which
R¹⁴ = CF₂CHF₂ and
R¹⁵ = as listed in Table (II-1).

Table (II-15)

Table (II-15) contains the compounds of the general formula (II), in which

R¹⁵ = as listed in Table (II-1).  

Table (II-16)

Table (II-16) contains the compounds of the general formula (II), in which
R¹⁴ = CN and
R¹⁵ = as listed in Table (II-1).

Table (II-17)

Table (II-17) contains the compounds of the general formula (II), in which
R¹⁴ = -OCH₂CF₃ and
R¹⁵ = as listed in Table (II-1).

Table (II-18)

Table (II-18) contains the compounds of the general formula (II), in which
R¹⁴ = -OCHF₂ and
R¹⁵ = as listed in Table (II-1).

Table (II-19)

Table (II-19) contains the compounds of the general formula (II), in which
R¹⁴ = Br and
R¹⁵ = as listed in Table (II-1).

Table (II-20)

Table (II-20) contains the compounds of the general formula (II), in which

R¹⁵ = as listed in Table (II-1).

Table (II-21)

Table (II-21) contains the compounds of the general formula (II), in which
R¹⁴ = Cl and
R¹⁵ = as listed in Table (II-1).

Table (II-22)

Table (II-22) contains the compounds of the general formula (II), in which
R¹⁴ = OCH₃ and
R¹⁵ = as listed in Table (II-1).

Table (II-23)

Table (II-23) contains the compounds of the general formula (II), in which
R¹⁴ = -OC₂H₅ and
R¹⁵ = as listed in Table (II-1).

Table (II-24)

Table (II-24) contains the compounds of the general formula (II) in which
R¹⁴ = -OC₃H₇-i and
R¹⁵ = as listed in Table (II-1).

Table (II-25)

Table (II-25) contains the compounds of the general formula (II), in which
R¹⁴ = -SCH₃ and
R¹⁵ = as listed in Table (II-1).

Table (II-26)

Table (II-26) contains the compounds of the general formula (II), in which
R¹⁴ = -SO₂CH₃ and
R¹⁵ = as listed in Table (II-1).

Table (II-27)

Table (II-27) contains the compounds of the general formula (II), in which
R¹⁴ = -SO₂C₂H₅ and
R¹⁵ = as listed in Table (II-I).

Table (II-28)

Table (II-28) contains the compounds of the general formula (II), in which
R¹⁴ = -SC₂H₅ and
R¹⁵ = as listed in Table (II-1).

Table (II-29)

Table (II-29) contains the compounds of the general formula (II), in which
R¹⁴ = -SC₃H₇-i and
R¹⁵ = as listed in Table (II-1).

Table (II-30)

Table (II-30) contains the compounds of the general formula (II), in which
R¹⁴ = -SCHF₂ and
R¹⁵ = as listed in Table (II-1).

Table (II-31)

Table (II-31) contains the compounds of the general formula (II), in which
R¹⁴ = -SCH₂CH₂CH₂F and
R¹⁵ = as listed in Table (II-1).

Table (II-32)

Table (II-32) contains the compounds of the general formula (II), in which
R¹⁴ = -OCH₂CH₂CH₂F and
R¹⁵ = as listed in Table (II-1).

Table (II-33)

Table (II-33) contains the compounds of the general formula (II), in which

R¹⁵ - as listed in Table (II-1).

Table (II-34)

Table (II-34) contains the compounds of the general formula (II), in which
R¹⁴ = CH₂CF₃ and
R¹⁵ - as listed in Table (II-1).

Table (II-35)

Table (II-35) contains the compounds of the general formula (II), in which

R¹⁵ = as listed in Table (II-1).  

Table (II-36)

Table (II-36) contains the compounds of the general formula (II), in which

R¹⁵ = as listed in Table (II-1).

Table (II-37)

Table (II-37) contains the compounds of the general formula (II), in which
R¹⁴ = -OCH₂CCl₃ and
R¹⁵ = as listed in Table (II-1).

Table (II-38)

Table (II-38) contains the compounds of the general formula (II), in which
R¹⁴ = -SCH₂Cl and
R¹⁵ = as listed in Table (II-1).

Table (II-39)

Table (II-39) contains the compounds of the general formula (II), in which
R¹⁴ = -SCH₂F and
R¹⁵ = as listed in Table (II-1).

Table (II-40)

Table (II-40) contains the compounds of the general formula (II), in which
R¹⁴ = -SCH₂CH₂F and
R¹⁵ = as listed in Table (II-1).

Table (II-41)

Table (II-41) contains the compounds of the general formula (II), in which
R¹⁴ = -SCH₂CHF₂ and
R¹⁵ = as listed in Table (II-1).

Table (II-42)

Table (II-42) contains the compounds of the general formula (II), in which
R¹⁴ = -SCH₂CF₃ and
R¹⁵ = as listed in Table (II-1).

Table (II-43)

Table (II-43) contains the compounds of the general formula (II), in which
R¹⁴ = -SCH₂CH₂CF₃ and
R¹⁵ = as listed in Table (II-1).

Table (II-44)

Table (II-44) contains the compounds of the general formula (II), in which
R¹⁴ = -SCH₂CH = CH₂ and
R¹⁵ = as listed in Table (II-1).

Table (II-45)

Table (II-45) contains the compounds of the general formula (II), in which
R¹⁴ = -SCH₂C≡CH and
R¹⁵ = as listed in Table (II-1).

Table (II-46)

Table (II-46) contains the compounds of the general formula (II), in which
R¹⁴ = -SCH = C = CH₂ and
R¹⁵ = as listed in Table (II-1).

Table (II-47)

Table (II-47) contains the compounds of the general formula (II), in which
R¹⁴ = -OCH₂CF₂CHF₂ and
R¹⁵ = as listed in Table (II-1).

Table (II-48)

Table (II-48) contains the compounds of the general formula (II), in which

R¹⁵ = as listed in Table (II-1).

Table (II-49)

Table (II-49) contains the compounds of the general formula (II) in which

R¹⁵ = as listed in Table (II-1).

The continue to carry out the method (a) as Halogen derivatives required as starting materials are general by the formula (III) Are defined. In this formula (III), R 11, R 12, R 13 and A 1 are preferably and particularly preferred for those residues that are already in connection with the Description of the compounds of formula (Ia) according to the invention as preferred and particularly preferred for these substituents. Hal is standing preferably for fluorine, chlorine or bromine, especially for fluorine or chlorine.

The halogen derivatives of the formula (III) are generally known compounds of organic chemistry or available in a generally known manner.

Those used to carry out process (b) according to the invention as starting materials required hydrazine derivatives are generally defined by the formula (IV). In of this formula (IV) R¹¹, R¹², R¹³ and A¹ are preferably and particularly preferred for those residues that are already in connection with the description Exercise of the compounds of formula (Ia) as preferred and were particularly preferred for these substituents.  

The hydrazine derivatives of the formula (IV) are known (cf., for example, US Pat. No. 4,127,575; US-PS 36 09 158; DE-OS 25 58 399; J. Chem. Soc. C; 1971, 167-174) or can be obtained in a simple manner by known processes (cf. e.g. Houben-Weyl "Methods of Organic Chemistry" Volume X / 2, p. 203, Thieme Verlag Stuttgart, 1967).

Formula (V) provides a general definition of the iminocarboxylic esters required as starting materials for carrying out process (b) according to the invention. In this formula (V) R²¹ and R²² independently of one another are preferably C₁-C₄-alkyl, in particular methyl or ethyl. R ^14-1 preferably or particularly preferably represents the meanings given above in connection with the description of the compounds of the formula (Ia) according to the invention in R¹⁴ for the corresponding substituents as preferred or particularly preferred.

The iminocarboxylic esters of the formula (V) are known or by known processes available (see e.g. Ber. 119, 2444-2457 [1986]; Bull. chem. Soc. Jpn. 55, 3943- 3944 [1982]; Chem. Lett. 1982, 1015-1016; Chem. Lett. 1987, 1403-1404; J. Amer. chem. Soc. 95, 3957-3963 [1973]; J. org. Chem. 36, 3251-3252 [1971]).

Those used to carry out process (c) according to the invention as starting materials N-aryl-1,2,4-triazolin-5-ones of the formula (Id) required are inventive Links.

Formula (VI) provides a general definition of the alkylating agents which are furthermore required as starting materials for carrying out process (c) according to the invention. In this formula (VI), R ^{15-1 is} preferably or particularly preferably the meanings mentioned above in connection with the description of the compounds of the formula (Ia) according to the invention in R¹⁵ for the corresponding substituents as preferred or particularly preferred. E represents a conventional electron-withdrawing leaving radical, for example halogen, in particular chlorine, bromine or iodine; or for each optionally substituted alkylsulfonyloxy, alkoxysulfonyloxy or arylsulfonyloxy, in particular for methanesulfonyloxy, trifluoromethanesulfonyloxy, methoxysulfonyloxy, ethoxysulfonyloxy or p-toluenesulfonyloxy.

The alkylating agents of formula (VI) are generally known compounds of Organic chemistry.

As a diluent for carrying out process (a) according to the invention inert organic solvents are suitable. These include in particular ali phatic, alicyclic or aromatic, optionally halogenated coal water substances such as gasoline, benzene, toluene, xylene, chlorobenzene, di chlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or Carbon tetrachloride; Ethers, such as diethyl ether, diisopropyl ether, dioxane, tetra hydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, Butanone or methyl isobutyl ketone; Nitriles, such as acetonitrile, propionitrile or Benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-Me thylformanilide, N-methylpyrrolidone or Hexamethylphosphorsäuretriamid or Esters, such as methyl acetate or ethyl acetate.

Process (a) according to the invention is preferably carried out in the presence of a suitable reaction auxiliary. As such, all the usual ones come inorganic or organic bases in question. These include, for example Alkaline earth or alkali metal hydroxides, such as sodium hydroxide, calcium hydroxide or potassium hydroxide, ammonium hydroxide, alkali metal carbonates such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate or sodium hydrogen carbon nate, ammonium carbonate, alkali or alkaline earth metal acetates, such as sodium acetate, Potassium acetate, calcium acetate or ammonium acetate, as well as tertiary amines, such as Trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-Me thylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabi cyclonones (DBN) or diazabicycloundecene (DBU), also piperidine.

The reaction temperatures can be carried out when carrying out the process according to the invention Process (a) can be varied over a wide range. Generally works one at temperatures between 0 ° C and + 180 ° C, preferably at temperatures between + 20 ° C and + 120 ° C.

Process (a) according to the invention is usually carried out under normal pressure guided. However, it is also possible to increase or decrease the pressure work.  

To carry out process (a) according to the invention, 1H- Triazolinone of formula (II) generally 1.0 to 3.0 mol, preferably 1.0 to 1.5 mol of halogen derivative of the formula (III) and optionally 1.0 to 3.0 mol, preferably 1.0 to 1.5 mol of base as a reaction auxiliary.

Carrying out the reaction, working up and isolating the reaction products takes place according to generally known methods (see also the manufacturer examples).

As a diluent for carrying out process (b) according to the invention inert organic solvents are suitable. Preferably used the description of the implementation of the method (a) added solvent.

The reaction temperatures can be carried out when carrying out the process according to the invention Process (b) can be varied over a wide range. Generally works one at temperatures between -20 ° C and + 150 ° C, preferably at temperature temperatures between 0 ° C and + 120 ° C.

Process (b) according to the invention is usually carried out under normal pressure guided. However, it is also possible to increase or decrease the pressure work.

The process (b) according to the invention is carried out per mole Hydrazine derivative of formula (IV) generally 1.0 to 3.0 moles, preferably 1.0 to 1.5 moles of iminocarboxylic ester of the formula (V).

Carrying out the reaction, working up and isolating the reaction products is carried out according to generally known methods.

As a diluent for carrying out process (c) according to the invention inert organic solvents are suitable. These include in particular ali phatic, alicyclic or aromatic, optionally halogenated coal water substances such as gasoline, benzene, toluene, xylene, chlorobenzene, dichlor benzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, tetrachlor carbon; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Nitriles such as acetonitrile, propio  nitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacet amide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamid; Esters such as methyl acetate or ethyl acetate or sulfoxides, such as dimethyl sulfoxide.

Method (c) according to the invention can optionally also be carried out in a two-pha system such as water / toluene or water / dichloromethane if necessary in the presence of a suitable phase transfer catalyst will. Examples of such catalysts are: tetrabutylammoni umiodide, tetrabutylammonium bromide, tetrabutylammonium chloride, tributyl-me thylphosphonium bromide, trimethyl-C₁₃ / C₁₅-alkylammonium chloride, trimethyl- C₁₃ / C₁₅-alkylammonium bromide, dibenzyl-dimethyl-ammonium methyl sulfate, dime thyl-C₁₂ / C₁₄-alkyl-benzylammonium chloride, dimethyl-C₁₂ / C₁₄-alkyl-benzylammo nium bromide, tetrabutylammonium hydroxide, triethylbenzylammonium chloride, Me thyltrioctylammonium chloride, trimethylbenzylammonium chloride, 15-crown-5, 18-crown-6 or tris [2- (2-methoxyethoxy) ethyl] amine.

Process (c) according to the invention is preferably used in the presence of a Neten reaction auxiliary carried out. As such come all the usual anorga African or organic bases in question. These include, for example, alkaline earth or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or -hydrogen carbonates, such as sodium hydride, sodium amide, sodium me ethylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, Sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, Potassium hydrogen carbonate or sodium hydrogen carbonate, ammonium hydroxide, Ammonium acetate or ammonium carbonate and tertiary amines such as trimethyl amine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperi din, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).

The reaction temperatures can be carried out when carrying out the process according to the invention Process (c) can be varied over a wide range. Generally works one at temperatures between -20 ° C and + 150 ° C, preferably at temperature temperatures between 0 ° C and + 120 ° C.  

Process (c) according to the invention is usually carried out under normal pressure guided. However, it is also possible to increase or decrease the pressure work.

To carry out process (c) according to the invention, Aryl-1,2,4-triazolin-5-one of the formula (Id) generally 1.0 to 3.0 mol, preferably as 1.0 to 2.0 moles of alkylating agent of formula (VI) and optionally 1.0 to 3.0 mol, preferably 1.0 to 2.0 mol, of base as reaction auxiliary.

Carrying out the reaction, working up and isolating the reaction products is carried out according to generally known methods.

The active compounds of the formula (I) which can be used according to the invention are suitable for good plant tolerance and favorable warm-blooded toxicity to control of animal pests, in particular insects, arachnids and nematodes, those in agriculture, in forests, in the protection of stocks and materials, and on occur in the hygiene sector. They can preferably be used as plant protection products be used. They are against normally sensitive and resistant types as well effective against all or individual stages of development. To the above Pests include:

From the order of the Isopoda z. B. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.

From the order of the Diplopoda z. B. Blaniulus guttulatus.

From the order of the Chilopoda z. B. Geophilus carpophagus, Scutigera spec.

From the order of the Symphyla z. B. Scutigerella immaculata.

From the order of the Thysanura z. B. Lepisma saccharina.

From the order of the Collembola z. B. Onychiurus armatus.

From the order of Orthoptera z. B. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria, Supella spp.

From the order of the Dermaptera z. B. Auricular Forficula.

From the order of the Isoptera z. B. Reticulitermes spp.  

From the order of the Anoplura z. B. Phylloxera vastatrix, Pemphigus spp., Phthirus spp., Pediculus spp., Haematopinus spp., Linognathus spp., Solenopotes spp.

From the order of the Mallophaga z. B. Trichodectes spp., Damalinea spp., Trimenopon spp., Monopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Felicola spp.

From the order of the Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci.

From the order of Heteroptera z. B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex spp., Rhodnius spp., Triatoma spp., Panstrongylus spp.

From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Sais setia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. Psylla spp.

From the order of the Lepidoptera z. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp. Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.

From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varive stis, Atomaria spp., Oryzaephilus surinamensis, Antho nomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes  spp., Cono derus spp., Melolontha melolontha, Amphimallon solsti tialis, Costelytra zealandica.

From the order of the Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Diptera z. B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Lucilia spp., Chrysomyia spp., Cuterebra spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, ceratitis capitata, Dacus oleae, Tipula paludosa, Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Muscina spp.

From the order of the Siphonapterida z. B. Xenopsylla spp., Ceratophyllus spp., Pulex spp., Ctenocephalides spp.

From the order of the Arachnida z. B. Scorpio maurus, Latrodectus mactans.

From the order of Acarina z. B. Myocoptes spp., Acarus siro, Argas spp., Ornithodoros spp., Ornithonyssus spp., Dermanyssus spp., Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Dermacentor spp., Haemaphysalis spp., Raillietia spp., Pneumonyssus spp., Sternostorma spp., Varroa spp., Otobius spp.

From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata) z. B .:
Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypppectoles spp ., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

The plant parasitic nematodes include z. B. Pratylenchus spp., Radopho lus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp.,  Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., xiphinema spp., Trichodorus spp.

The active ingredients which can be used according to the invention are notable in particular a high insecticidal effectiveness.

They can be used with particularly good success to combat plant-damaging leaf and soil insects, for example against the larvae of the horseradish leaf beetle (Phaedon cochleariae) or against the larvae of the green Rice leafhopper (Nephotettix cincticeps) against the caterpillars of the cockroach (Plutella maculipennis), also against caterpillars of the owl butterfly (Spodoptera rugiperda) and against the tobacco bud caterpillar (Heliothis virescens).

Furthermore, the active compounds of the formula (I) which can be used according to the invention have also an acaricidal and a fungicidal action, for example against Pyricularia oryzae on rice.

The active ingredients can be converted into the usual formulations, such as Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated nated natural and synthetic substances as well as very fine encapsulation in polymers Fabrics.

These formulations are prepared in a known manner, e.g. B. by Ver mixing the active ingredients with extenders, i.e. liquid solvents and / or solid carriers, optionally using surface-active agents Agents, that is emulsifiers and / or dispersants and / or foam generators resources.

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic carbons Hydrogen, such as cyclohexane or paraffins, e.g. B. petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and their ethers and Esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclo  hexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfate oxide, as well as water.

The following are suitable as solid carriers:
e.g. B. ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: z. B. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic u 26294 00070 552 001000280000000200012000285912618300040 0002019521162 00004 26175nd organic flours as well as granules from organic material such as sawdust, coconut and tobacco husks; as emulsifying and / or foam-generating agents come into question: z. B. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; as dispersing agents come into question: z. B. lignin sulfite and methyl cellulose.

In the formulations, adhesives such as carboxymethyl cellulose, natural Liche and synthetic powdery, granular or latex-shaped polymers used such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural Phospholipids such as cephalins and lecithins and synthetic phospholipids. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, Ferrocyan blue and organic dyes such as alizarin, azo and metal phthalalo cyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, Cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95% by weight Active ingredient, preferably between 0.5 and 90%.

The active ingredient according to the invention can be in its commercially available formulations as well as in the use forms prepared from these formulations in Mix with other active ingredients, such as insecticides, attractants, sterilants, Bactericides, acaricides, nematicides, fungicides, growth-regulating substances fen or herbicides. The insecticides include, for example, Phos  phosphoric esters, carbamates, carboxylic esters, chlorinated hydrocarbons, Phe nylureas, substances produced by microorganisms u. a.

Particularly cheap mixing partners are e.g. B. the following:

Fungicides

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ′, 6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanide; 2,6-di chloro-N- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinoline sulfate; Methyl- (E) -2- {2- [6- (2-cyano phenoxy) pyrimidin-4-yloxy] phenyl} -3 methoxyacrylate; Methyl (E) methoximino [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,
Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupirimate, Buthiobate,
Calcium polysulfide, captafol, captan, carbendazim, carboxin, quinomethionate (quinomethionate), chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazole, cyprofuram,
Dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodine, drazoxolone,
Edifenphos, epoxyconazole, ethirimol, etridiazole,

Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fen propimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam, Fludi oxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanil, Fulinolide, Flu triafolide , Furalaxyl, Furmecyclox,
Guazatine,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodione, Isoprothiolan,
Kasugamycin, copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metsulfovax, Myclobutanil,
Nickel dimethyldithiocarbamate, Nitrothal-isopropyl, Nuarimol, Ofurace, Oxadixyl, Oxamocarb, Oxycarboxin,
Pefurazoate, penconazole, pencycuron, phosdiphen, phthalide, pimaricin, piperalin, polycarbamate, polyoxin, probenazole, prochloraz, procymidon, propamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon,
Quintozen (PCNB),
Sulfur and sulfur preparations,
Tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, Thicyofen, thiophanate-methyl, thiram, Tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
Validamycin A, vinclozolin,
Zineb, ziram.

Bactericides

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, Kasugamy cin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, Tecloftalam, copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides

Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alpha methrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,
Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyluthrin, Bifen thrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chlorethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorfluazu ron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocytoshrin, Cyclothrin, Clothrinin Cyhalothrin, cyhexatin, cyper methrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazi non, Dichlorfenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,
Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Etho prophos, Etrimphos,

Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipro nil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Fufionatexfonophon, Fufionproxophon, Fufonproxophone, Fufonproxophon, Fufonproxophon, Fufonfox, Fufionfox, Fufionfox, Fufone
HCH, heptenophos, hexaflumuron, hexythiazox,
Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lambda-cyhalothrin, Lufenuron,
Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
Naled, NC 184, NI 25, Nitenpyram,
Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophhine, Pyrachlophhion, Pyrachlophion, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophion Pyridaben, pyrimidifen, pyriproxifen,
Quinalphos,
RH 5992,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,
Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiome thon, Thionazin, Thuringiensin, Tralomenhronon, Triaromenhriazonium, Triaromenhroniazonium
Vamidothione, XMC, xylylcarb, YI 5301/5302, zetamethrin.

Herbicides

For example anilides, such as. B. Diflufenican and Propanil; Aryl carboxylic acids, such as e.g. B. dichloropicolinic acid, dicamba and picloram; Aryloxyalkanoic acids, such as. B. 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy phenoxy-alkanoic acid esters, such as. B. Diclofop-methyl, fenoxaprop-ethyl, fluazifop butyl, haloxyfop-methyl and quizalofop-ethyl; Azinones, such as B. Chloridazon and Norflurazon; Carbamates, e.g. B. chlorpropham, desmedipham, phenmedipham and propham; Chloroacetanilides such as e.g. B. alachlor, acetochlor, butachlor, Metazachlor, metolachlor, pretilachlor and propachlor; Dinitroanilines such as e.g. B. Oryzalin, pendimethalin and trifluralin; Diphenyl ether, such as. B. Acifluorfen, Bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; Ureas, such as B. chlorotoluron, diuron, fluometuron, isoproturon, linuron and Methabenzthiazuron; Hydroxylamines, such as. B. Alloxydim, Clethodim, Cyclo xydim, Sethoxydim and Tralkoxydim, Imidazolinone, such as. B. Imazethapyr,  Imazamethabenz, imazapyr and imazaquin; Nitriles such as B. bromoxynil, dichlor benil and ioxynil; Oxyacetamides such as e.g. B. Mefenacet; Sulfonylureas, such as. B. Amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfu ron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, Thi fensulfuron-methyl, triasulfuron and tribenuron-methyl; Thiol carbamates such as e.g. B. Butylates, Cycloates, Diallates, EPTC, Esprocarb, Molinate, Prosulfocarb, Thio bencarb and triallates; Triazines, e.g. B. Atrazin, Cyanazin, Simazin, Simetryne, Terbutryne and terbutylazin; Triazinones such as e.g. B. hexazinone, metamitron and Metribuzin; other, such as B. aminotriazole, benfuresate, bentazone, cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorochloridone, Glufosinate, Glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and tridiphanes.

The active ingredient according to the invention can also be in its commercially available form formulations and in the application forms prepared from these formulations in a mixture with synergists. Synergists are connections through which the effect of the active ingredients is increased without the added synergist must be actively active itself.

The active ingredient content of the prepared from the commercially available formulations Application forms can vary widely. The drug concentration the use forms can be from 0.0000001 to 95% by weight of active ingredient, preferably between 0.0001 and 1% by weight.

The application takes place in a customary manner adapted to the application forms Wise.

When used against hygiene and storage pests, the stands out Active ingredient through an excellent residual effect on wood and clay as well due to good stability to alkali on limed substrates.

The active compounds according to the invention act not only against plant and hygiene and storage pests, but also against in the veterinary sector animal parasites (ectoparasites) such as tortoise ticks, leather ticks, mite mites, Running mites, flies (stinging and licking), parasitic fly larvae, lice, Hair lice, featherlings and fleas. For example, they show excellent Efficacy against ticks, such as Boophilus microplus.  

The active compounds of the formula (I) according to the invention are also suitable for combating treatment of arthropods, the farm animals, such as. B. cattle, sheep, Goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, Geese, bees, other pets such as B. dogs, cats, house birds, aqua reindeer fish and so-called experimental animals, such as B. hamsters, guinea pigs, Infect rats and mice. By fighting these arthropods are said to Deaths and reduced performance (for meat, milk, wool, skins, eggs, Honey, etc.) can be reduced, so that by using the invention Active ingredients a more economical and easier animal husbandry is possible.

The active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, Ta Bletten, capsules, watering, drenching, granules, pastes, boluses, the feed-through Method, of suppositories, by parenteral administration, such as by injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), Implan tate, by nasal application, by dermal application in the form, for example of diving or bathing (dipping), spraying (spray), pouring on (pour-on and Spot-on), washing, powdering and with the help of active ingredients Shaped bodies, such as collars, ear tags, tail tags, limb straps, Holders, marking devices, etc.

When used for cattle, poultry, pets etc. you can use the active ingredients of the formula (I) as formulations (for example powders, emulsions, flowable Agents), which contain the active ingredients in an amount of 1 to 80 wt .-%, directly or after 100 to 10,000-fold dilution, or as a chemical Use bath.

The manufacture and use of the active compounds according to the invention start out the following examples.

Manufacturing examples example 1

(Method a)

3.86 g (0.02 mol) of 3-trifluoromethyl-4-propenyl-1H-1,2,4-triazolin-5-one and 2.76 g (0.02 mol) potassium carbonate in 100 ml of dimethyl sulfoxide Room temperature with 5.41 g (0.02 mol) of 2,6-dinitro-4-trifluoromethyl-chlorobenzene mixed and stirred for 4 hours at 80 ° C and 1 hour at 120 ° C. For Working up, the reaction mixture is stirred with ice water, the precipitated Aspirated product and this recrystallized from isopropanol.

4.4 g (52% of theory) of 1- (2,6-dinitro-4-trifluoromethyl-phenyl) -3- are obtained. trifluoromethyl-4-propenyl-1,2,4-triazolin-5-one with a melting point of 136 ° C.  

Analogous to Example 1 and in accordance with the general description of the inventions Manufacturing processes according to the invention can be carried out in Table 1 below Compounds of formula (Ia) listed.

Table 1

Examples of use

The following application examples list the following Compounds used as reference substances:

1- (2,6-dichloro-4-trifluoromethylphenyl) -3-methyl-4-methylamino-1,2,4 - triazolin-5- on

1- (2,6-dichloro-3-fluoro-4-trifluoromethyl-phenyl) -3-methyl-4-methylamino-no-1,2,4- triazolin-5-one

1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyclopropyl-4-methylamino - 1,2,4-triazolin-5-one
(all known from EP-A 0 617 026, (A) = Ex. 44, (B) = Ex. 45, (C) = Ex. 72).

Example A Phaedon larval test

Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent and the specified given amount of emulsifier and dilute the concentrate with water to the ge wanted concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with horseradish leaf beetle larvae (Phaedon cochleariae) occupied while the leaves are still moist.

After the desired time, the kill is determined in%. Here means 100% that all beetle larvae have been killed; 0% means that no beetles Larvae were killed.

In this test, e.g. B. the compounds of Preparation Examples 5, 8, 11, 12, 13, 15, 21, 27, 36, 42, 45, 50, 57 and 83 for an exemplary active ingredient concentration of 0.1% after 7 days a kill of 100%, while the known compounds (B) and (C) show no or a 10% kill.  

Example B Plutella test

Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent and the specified amount of emulsifier and dilute the concentrate with water to the wanted concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with caterpillars Plutella macuhpennis occupied while the leaves are still moist.

After the desired time, the kill is determined in%. 100 means % that all caterpillars have been killed; 0% means that no caterpillars are killed were.

In this test, e.g. B. the compounds of Preparation Examples 4, 5, 12, 21, 22, 32, 49 and 81 with an exemplary active ingredient concentration of 0.1% after 7 days a 100% kill, while the known compound (C) shows a 5% kill.  

Example C Spodoptera Frugiperda test

Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent and the specified amount of emulsifier and dilute the concentrate with water to the desired concentration wanted concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with caterpillars of the owl butterfly Spodoptera frugiperda occupied while the leaves are still moist.

After the desired time, the effect is determined in%. Here means 100% that all caterpillars have been killed; 0% means that no caterpillars were killed.

In this test, e.g. B. the compounds of Preparation Examples 10, 12, 21, 49 and 50 with an exemplary active ingredient concentration of 0.1% according to FIG. 7 Days a kill of 100%, while the known compound (C) none Shows effect.  

Example D Heliothis virescens test

Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent and the specified amount of emulsifier and dilute the concentrate with water to the wanted concentration.

Soybean shoots (Glycine max) are dipped into the active ingredient preparation desired concentration treated and with the tobacco bud caterpillar Heliothis virescens occupied while the leaves are still moist.

After the desired time, the kill is determined in%. 100 means % that all caterpillars have been killed; 0% means that no caterpillars are killed were.

In this test, e.g. B. the compounds of Preparation Examples 4 and 5 with an exemplary active ingredient concentration of 0.1% after 6 days an Ab killing of 100%, while the known compounds (A) and (B) none Show effects.  

Example E Nephotettix test

Solvent: 7 parts by weight?
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent and the specified amount of emulsifier and dilute the concentrate with water to the wanted concentration.

Rice seedlings (Oryza sativa) are dipped into the active ingredient preparation the desired concentration and treated with green rice leafhopper larvae Nephotettix cincticeps populates while the seedlings are still moist.

After the desired time, the kill is determined in%. 100 means % that all cicadas have been killed; 0% means that no cicadas are killed were.

In this test, e.g. B. the compounds of Preparation Examples 12, 31, 41, 45 and 58 with an exemplary active ingredient concentration of 0.1% according to 6 Days a mortality of 90 to 100%, while the known compounds (A), (B) and (C) show no effect.  

Example F Test with Boophilus microplus resistant / SP-resistant Parkhurst strain

Test animals: adult sucked females
Solvent: dimethyl sulfoxide

20 mg of active ingredient are dissolved in 1 ml of dimethyl sulfoxide, low concentrations are made by diluting in the same solvent.

The test is carried out in 5-fold determination, 1 μl of the solution is added to the Abdomen injected, the animals transferred into bowls and in an air-conditioned Saved space. The effect is determined by the inhibition of egg laying. 100% means that no tick has laid.

In this test, e.g. B. the compounds of the invention Production examples 5, 21, 32, 33, 34 and 36 for an exemplary active ingredient concentration of 20 µg a 100% effect, while the well-known verbin (A), (B) and (C) have no effect.  

Example G Cockroach test

Test animals: Periplaneta americana
Solvent: 35 parts by weight of ethylene glycol monomethyl ether
Emulsifier: 35 parts by weight of nonylphenol polyglycol ether

Three weights are mixed to prepare a suitable formulation parts of active ingredient with seven parts of the solvent emulsifier specified above Mix and dilute the emulsion concentrate thus obtained with water to desired concentration.

2 ml of this active ingredient preparation are placed on filter paper discs (⌀ 9.5 cm) pipetted, which are in Petri dishes of appropriate size. After drying of the filter discs, 5 test animals P. americana are transferred and covered.

After 3 days, the effectiveness of the active ingredient preparation is determined. Here means 100% that all cockroaches have been killed; 0% means that none Cockroaches were killed.

In this test, e.g. B. the compounds of the invention Production examples 4, 5, 12, 21, 27, 28, 32, 36, 41 and 50 in one exemplary active ingredient concentration of 1000 ppm a 100% effect, while the known compounds (A), (B) and (C) show no effect.  

Example H Test with flies (Musca domestica)

Test animals: adult Musca domestica, Reichswald strain (OP, SP, carbamate-resistant)
Solvent: 35 parts by weight of ethylene glycol monomethyl ether
Emulsifier: 35 parts by weight of nonylphenol polyglycol ether

Three weights are mixed to prepare a suitable formulation parts of active ingredient with seven parts of the solvent emulsifier specified above Mix and dilute the emulsion concentrate thus obtained with water to desired concentration.

2 ml of this active ingredient preparation are placed on filter paper dishes (⌀ 9.5 cm) pipetted, which are in Petri dishes of appropriate size. After drying of the filter disks, 25 test animals are transferred to the Petri dish and covered.

After 1, 3, 5 and 24 hours, the effectiveness of the drug preparation determined. 100% means that all flies have been killed; 0% means that no flies were killed.

In this test, e.g. B. the compounds of the invention Production examples 4, 5, 8, 12, 21, 22, 23, 24, 28, 32, 33 and 36 in one exemplary active ingredient concentration of 100 ppm a 100% effect, while the known compounds (A), (B) and (C) show no effect.  

Example I Test with fly larvae / development-inhibiting effect

Test animals: All larval stages of Lucilia cuprina (OP-resistant) [dolls and adults (without contact with the active ingredient)]
Solvent: 35 parts by weight of ethylene glycol monomethyl ether
Emulsifier: 35 parts by weight of nonylphenol polyglycol ether

Three Ge are mixed to produce a suitable formulation important parts of active ingredient with seven parts of the solvent Emulsifier mixture and dilutes the emulsion concentrate thus obtained with Water to the desired concentration.

30-50 larvae per concentration are on horses in glass tubes meat (1 cm³) brought to which 500 µl of the dilution to be tested be pipetted. The glass tubes are placed in plastic cups Floor is covered with sea sand, and in an air-conditioned room (26 ° C ± 1.5 ° C, 70% relative humidity ± 10%). The effects are checked after 24 Hours and 48 hours (lervicidal activity). After the larvae emigrate (approx. 72 hours) the glass tubes are removed and perforated plastic lids put on the mug. After 1½ times the development period (hatching of the control flies), the hatched flies and the dolls / doll covers are counted.

The criterion for the effect is the occurrence of death in the treated lar ven after 48 hours (larvicidal effect), or the inhibition of adult hatching from the dolls or the inhibition of doll formation. As a criterion for the in in vitro effect of a substance applies to the inhibition of flea development, or a Developmental standstill before the adult stage. 100% means larvicidal Effect that all larvae have died after 48 hours. 100% development lungsinhibitory effect means that no adult flies have hatched.

In this test, e.g. B. the compounds of the invention Preparation examples 4, 5, 8, 12, 21, 33, 42 and 50 for an active ingredient concentration tration of 1000 ppm a 100% effect, while the well-known verbin (A), (B) and (C) have no effect.

Claims (7)

1. Agent for controlling animal pests, characterized in that it contains at least one compound of the formula (I) in which
A represents nitrogen or the group CR,
R represents hydrogen, halogen, nitro, cyano, hydroxyl, alkyl which is optionally substituted by halogen, cyano, nitro, alkoxy or amino, optionally substituted cycloalkyl or the radical -CX-NY¹Y²,
R¹ is halogen, nitro, cyano, in each case alkyl or alkoxy optionally substituted by halogen, cyano, nitro, alkoxy or amino, optionally substituted cycloalkyl or the radical -CX-NY¹Y²,
R² represents hydrogen, halogen, alkyl which is optionally substituted by halogen, cyano, nitro, alkoxy or amino or optionally substituted cycloalkyl,
R³ represents nitro, haloalkyl, haloalkoxy or the radical -S (O) _n R⁶,
R⁴ for halogen, nitro, cyano, each optionally substituted by halogen, cyano, nitro, alkoxy or amino-substituted alkyl or alkoxy, for alkenyl, alkenyloxy, alkynyl, hydroxy, mercapto, each optionally substituted cycloalkyl or cycloalkylalkyl, each optionally substituted aryl, aryloxyalkyl or aralkyl or the radical -S (O) _n R⁶,
R⁵ for hydrogen, cyano, each optionally substituted by halogen, cyano, nitro, alkoxy or amino-substituted alkyl or alkoxy, for alkenyl, alkenyloxy, alkynyl, alkynyloxy, in each case optionally substituted cycloalkyl or cycloalkylalkyl, in each case optionally substituted aryl or aralkyl or one of the Radicals -S (O) _n R⁶, -NR⁷R⁸ or -N = CR⁹R¹⁰,
R⁶ represents alkyl optionally substituted by halogen, cyano, nitro, alkoxy or amino, alkenyl, alkanedienyl, alkynyl, optionally substituted cycloalkyl or optionally substituted aryl,
R⁷ represents hydrogen, optionally substituted by halogen, cyano, nitro, alk oxy or amino-substituted alkyl, alkenyl, alkynyl, alkoxy, optionally substituted cycloalkyl or optionally substituted aryl,
R⁸ represents hydrogen, optionally substituted by halogen, cyano, nitro, alkoxy or amino, represents alkenyl, alkynyl, alkoxy, optionally substituted cycloalkyl or optionally substituted aryl,
R⁷ and R⁸ together with the nitrogen atom to which they are attached represent an optionally substituted heterocycle which optionally contains one or more further heteroatoms,
R⁹ represents hydrogen, optionally substituted by halogen, cyano, nitro, alk oxy or amino-substituted alkyl, by alkoxy, optionally substituted cycloalkyl or in each case optionally substituted aryl or heterocyclyl,
R¹⁰ represents hydrogen, optionally substituted by halogen, cyano, nitro, alk oxy or amino alkyl, alkoxy, optionally substituted cycloalkyl or in each case optionally substituted aryl or heterocyclyl,
X represents oxygen or sulfur,
Y¹ represents hydrogen or alkyl,
Y² represents hydrogen or alkyl and
n stands for one of the numbers 0, 1 or 2. 2. A method for controlling animal pests, thereby records that compounds of formula (I) according to claim 1 Pests and / or their habitat. 3. Use of compounds of formula (I) according to claim 1 for loading control of animal pests. 4. Process for the preparation of pesticides, thereby ge indicates that compounds of the formula (I) according to Claim 1 mixed with extenders and / or surface-active substances. 5. Use of compounds of formula (I) according to claim 1 for the preparation provision of pesticides. 6. Compounds of formula (Ia) in which
A¹ represents nitrogen or the group CR ^O ,
R ^{O represents} hydrogen, halogen, nitro, cyano, hydroxyl, alkyl which is optionally substituted by halogen, cyano, nitro, alkoxy or amino, optionally substituted cycloalkyl or the radical -CX¹-NY¹¹Y¹²,
R¹¹ represents halogen, nitro, cyano, in each case alkyl or alkoxy optionally substituted by halogen, cyano, nitro, alkoxy or amino, optionally substituted cycloalkyl or the radical -CX¹-NY¹¹Y¹²,
R 12 represents hydrogen, halogen, alkyl which is optionally substituted by halogen, cyano, nitro, alkoxy or amino or optionally substituted cycloalkyl,
R¹³ represents nitro, haloalkyl, haloalkoxy or the radical -S (O) _n ¹R¹⁶,
R¹⁴ for halogen, cyano, each optionally substituted by halogen, cyano, nitro, alkoxy or amino-substituted alkyl or alkoxy, for alkenyl, alkenyloxy, alkynyl, hydroxy, mercapto, in each case optionally substituted cycloalkyl or cycloalkylalkyl, in each case optionally substituted aryl, aryloxyalkyl or aralkyl or the radical -S (O) _n ¹R¹⁶,
R¹⁵ for hydrogen, cyano, amino, each optionally substituted by halo gene, cyano, nitro, alkoxy or amino-substituted alkyl or alkoxy, for alkenyl, alkenyloxy, alkynyl, alkynyloxy, in each case optionally substituted cycloalkyl or cycloalkylalkyl, each optionally substituted aryl or aralkyl or is one of the radicals -S (O) _n ¹R¹⁶, -NR¹⁷R¹⁸ or -N = CR¹⁹R²⁰,
R¹⁶ represents alkyl optionally substituted by halogen, cyano, nitro, alkoxy or amino, alkenyl, alkanedienyl, alkynyl, optionally substituted cycloalkyl or optionally substituted aryl,
R¹⁷ and R¹⁸ together with the nitrogen atom to which they are attached represent an optionally substituted heterocycle which optionally contains one or more further heteroatoms,
R¹⁹ represents hydrogen, optionally substituted by halogen, cyano, nitro, alk oxy or amino alkyl, alkoxy, optionally substituted cycloalkyl or in each case optionally substituted aryl or heterocyclyl,
R²⁰ represents hydrogen, optionally substituted by halogen, cyano, nitro, alk oxy or amino, represents alkoxy, optionally substituted cycloalkyl or in each case optionally substituted aryl or heterocyclyl,
X¹ represents oxygen or sulfur,
Y¹¹ represents hydrogen or alkyl,
Y¹² represents hydrogen or alkyl and
n¹ represents one of the numbers 0, 1 or 2. 7. A process for the preparation of compounds of formula (Ia) according to claim 6, characterized in that to obtain

• a) compounds of the formula (Ia) in which
  R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and A¹ have the meaning given above,
  1H-triazolinones of the formula (II) in which
  R¹⁴ and R¹⁵ have the meaning given above,
  with halogen derivatives of the formula (III) in which
  R¹¹, R¹², R¹³ and A¹ have the meaning given above and
  Hal stands for halogen,
  if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary;
• b) compounds of the formula (Ib) in which
  R¹¹, R¹², R¹³ and A¹ have the meaning given above and
  R ^{14-1 represents} cyano, in each case optionally substituted by halogen, cyano, nitro, alkoxy or amino, alkyl or alkoxy, represents alkenyl, alkenyloxy, alkynyl, in each case optionally substituted cycloalkyl or cycloalkylalkyl or in each case optionally substituted aryl, aryloxyalkyl or aralkyl,
  Hydrazine derivatives of the formula (IV) in which
  R¹¹, R¹², R¹³ and A¹ have the meaning given above,
  with imino carboxylic esters of the formula (V) in which
  R ^{14-1 has} the meaning given above and
  R²¹ and R²² independently of one another are alkyl (preferably C₁-C₈-alkyl),
  in the presence of a diluent;
• c) compounds of the formula (Ic) in which
  R¹¹, R¹², R¹³, R¹⁴ and A¹ have the meaning given above and
  R ^{15-1 represents} cyano, alkyl which is optionally substituted by halogen, cyano, nitro, alkoxy or amino, alkenyl, alkynyl, in each case optionally substituted cycloalkyl and cycloalkylalkyl or optionally substituted aryl,
  N-aryl-1,2,4-triazolin-5-ones of the formula (Id) in which
  R¹¹, R¹², R¹³, R¹⁴ and A¹ have the meaning given above,
  with alkylating agents of the formula (VI) ER ^15-1 (VI) in which
  R ^{15-1 has} the meaning given above and
  E represents an electron-withdrawing leaving group,
  if appropriate in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary.